190 °C (374 °F; 463 K) (decomposes) (mixed isomers), 173 °C (cis and trans isomers)
Acidity (pKa)
2.80, 4.46 (trans isomer)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound
Aconitic acid is an organic acid. The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerization of citrate to isocitrate in the citric acid cycle. It is acted upon by the enzyme aconitase.
Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid:[3]
(HO2CCH2)2C(OH)CO2H → HO2CCH=C(CO2H)CH2CO2H + H2O
A mixture of isomers are generated in this way.
Aconitic acid was originally isolated from Aconitum napellus by Swiss chemist and apothecary Jacques Peschier in 1820.[4][5] It was first prepared by thermal dehydration.[6]
^Dawson, R. M. C.; Elliott, D. C.; Elliott, W. H. (1989). Data for Biochemical Research (3rd ed.). Oxford: Clarendon Press. ISBN 9780198552994.
^Bruce, W. F. (1937). "Aconitic Acid". Organic Syntheses. 17: 1. doi:10.15227/orgsyn.017.0001.
^Brande, William Thomas (1848). A Manual of Chemistry, Vol II (6 ed.). London: John W. Parker. p. 1344. Retrieved 8 November 2023.
^Reichenbach, Karl-Rudolf (2001). Jacques Peschier (1769-1832): Ein Genfer Apotheker und Chemiker. Zürich: Wissenschaftliche Verlagsgesellschaft mbH Stuttgart. ISBN 3804719090. Retrieved 8 November 2023.
^Pawolleck, B. (1875). "Substitutionsproducte der Citronensäure und ein Versuch zur Synthese der letzteren" [Substitution products of citric acid and an attempt at the synthesis of the latter]. Justus Liebig's Annalen der Chemie. 178 (2–3): 150–170. doi:10.1002/jlac.18751780203.
closely related acids isocitric acid, aconiticacid, and propane-1,2,3-tricarboxylic acid (tricarballylic acid, carballylic acid) Acids in wine This still...
The citric acid cycle—also known as the Krebs cycle, Szent–Györgyi–Krebs cycle or the TCA cycle (tricarboxylic acid cycle)—is a series of biochemical reactions...
itaconic acid. Cis-aconiticacid spontaneously converts to its thermodynamically more stable (see chemical stability) isomer, trans-aconiticacid, at pH...
Carboxylic acids are organic acids characterized by a carboxyl (-COOH) functional group. The naming of these compounds is governed by IUPAC nomenclature...
tricarboxylic acid is citric acid. Citric acid, a type of tricarboxylic acid, is used in the citric acid cycle – also known as tricarboxylic acid (TCA) cycle...
Homoaconitatic acid (homoaconitate) is related to aconiticacid but with one extra carbon. It is part of the α-aminoadipate pathway for lysine biosynthesis...
poisonous, containing cardiostimulant compounds, such as adonidin and aconiticacid. Infusions of the plant are used in the medicine Bekhterev's mixture...
Martynov, A. V. (2005-12-06). "New Approach to the Synthesis of trans-AconiticAcid Imides". ChemInform. 36 (49): no. doi:10.1002/chin.200549068. ISSN 1522-2667...
Enrichment and isolation of rumen bacteria that reduce trans-aconiticacid to tricarballylic acid. Appl. Env. Microbiol. 49: 120-126. Schwartz, R., M. Topley...
cis-aconitate in the tricarboxylic acid cycle, a non-redox-active process. Citric acidAconiticacid Isocitric acid Aconitase, displayed in the structures...
commonly used in industry to produce important organic acids, such as itaconic acid and cis-aconiticacid, as well as enzymes, like xylanase. It was also the...
subsequently used for the generation of the Krebs cycle intermediates aconitic and isocitric acids. Maleic anhydride dimerizes in a photochemical reaction to form...
"The Isolation and Characterization of β-N-Oxalyl-L-α,β-diaminopropionic acid: A Neurotoxin from the Seeds of Lathyrus sativus". Biochemistry. 3 (3): 432–436...
(1957). "Biosynthesis of itaconic acid in Aspergillus terreus. III. The properties and reaction mechanism of cis-aconiticacid decarboxylase". J. Biol. Chem...
Japanese medicine. The seed contains cis-aconitic anhydride ethyl ester and cis-2,4,5-trihydroxycinnamic acid. English Names for Korean Native Plants (PDF)...
says that Des had a more extreme idea for Martin O'Brien's speech - mixing acid into the paint that would be thrown. Later that night, Blake tells Mattie...
methionine, glycine, β-aminobutyric acid, γ-aminobutyric acid, ephedrine, trigonelline, phytosterols and glucoronic acid. Care should be taken as crow dipper...
stepmothers mix lurid aconites. Aconitine was also made famous by its use in Oscar Wilde's 1891 story "Lord Arthur Savile's Crime". Aconite also plays a prominent...
Chemicals such as arsenic, strychnine, corrosive sublimate, aconitum and prussic acid were allegedly involved. There are no cases of convictions being reported...
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